If two Ensnaring Strikes affect the same target, does it have to make two saves to be unrestrained?

Question

Say two Rangers shot the same target with ensnaring strike and the target failed its saves on both.

The PHB says the effects of the same spell cast multiple times don't combine such as two Clerics casting bless on the same target only provides the benefits once. (pg 205)

My understanding is there are still two spells in effect. So for my example above, if the target succeeded on its Strength save and removed one ensnaring strike, it would still be restrained and damaged by the other.

Are there examples where this is talked about per RAW?

Answer 1

Two separate saves (if the strongest/most recent spell ends).

While both spells are maintained, the most potent or most recent one is active.

The effects of the same spell cast multiple times don't combine, however. Instead, the most potent effect - such as the highest bonus - from those castings applies while their durations overlap, or the most recent effect applies if the castings are equally potent and their durations overlap.

Ensnaring strike (PHB, p. 237) reads

While restrained by this spell, the target takes 1d6 piercing damage at the start of each of its turns. The creature restrained can make a Strength check against your spell save DC. On a success, the target is freed.

So, while both spells are maintained, the strongest ensnaring strike is active, restraining and damaging the target, while the weakest one is suppressed (but still on-going, and its caster is still maintaining concentration). When the target succeeds on a save, the target is freed from that spell. The spell hasn't finished (lasts 1 minute), but its caster can dismiss it at any time, since it is a concentration spell, and is now useless (no longer doing damage or restraining a target, it's just wasting concentration).

If the weaker spell is still being maintained (less than a minute has passed since it was cast, and the caster has not lost concentration) when the most potent spell ends (its caster dropped concentration, or its duration ran out), the weaker spell is now active, restraining and damaging the target, which requires another save.

Someone has pointed out (in a now deleted comment below) how the spell says the target is freed and not the spell ends. You can argue that "getting freed" would release you from any other restraint, but I think it makes no sense that the target gets freed from all restraints and incapacitates affecting it. If you had your Brawler Barbarian grappling and restraining a target, would his getting rid of Ensnaring Strike also free him from the Barbarian? It seems clear to me the idea is that making your save frees you from the effects of this spell, and nothing else.

Answer 2

They only have to make one save because they are only under one effect (unless the most potent spell ends)

When a creature is under the effects of two of the same spell, only one of them takes effect at a time: the most potent or recent one. From "Combining Magical Effects" in the PHB:

The effects of the same spell cast multiple times don't combine, however. Instead, the most potent effect — such as the highest bonus — from those castings applies while their durations overlap, or the most recent effect applies if the castings are equally potent and their durations overlap.

When the creature successfully makes their save against the most potent spell, that spell is still active and would still override the other spell. From the description of ensnaring strike (PHB, p. 237):

A creature restrained by the vines or one that can touch the creature can use its action to make a Strength check against your spell save DC. On a success, the target is freed.

Making one save would free them from the only spell effect currently affecting them (the most potent one). And since the spell does not end on that successful save and no other spell becomes more potent than it, its effects remain. Thus, they would have to make only one save.

Ending the most potent spell after the successful save would cause the creature to have to make another save

If the most potent spell ends for any reason then the less potent spell effect (if still present) would take effect. The natural way for this to happen is going to be the duration of the first spell cast expiring. One way to purposefully do this is to have the caster of the most potent spell (that just got saved against) stop concentrating on the spell and thus end it. No matter how, when the most potent spell ends, the other spell (the formerly less potent one) would be able to take effect and the creature would then have to make that save as well in order to no longer be restrained by the effects of this spell.

Since a creature can stop concentrating on a spell at any time this is allowed in the rules. With ensnaring strike there is no reason not to do this since the spell no longer has any effect.